File Could Not Be Found - But it's in the collectio

A fews songs specifically are giving me the orange check mark. I have removed all missing files, deleted and re-added the songs into the collection. They will play in the collection, in the iTunes drop down, in iTunes themselves, and will even load with my cue points. However when I drag these newly sourced files over to my external hard drive I still get the error message that the file can not be found. I have relocated all of the files through the finder window search that appears. I need help figuring out why the songs will not transfer over to my thumb drive before I throw my computer out the window please. I have absolutely 0 idea what else to do. I'm on a Mac OSX 10.14.6, rekordbox 6.5.